Profile | How entrepreneur and social media star Simon Squibb is helping people achieve their dreams

With 17 million followers and over 500 million monthly views across his social media platforms, Simon Squibb has built an audience most influencers can only dream of. He has become one of the world’s most influential voices in the realm of entrepreneurship, largely down to his approach – which is far from boring or didactic. His viral short videos – one has an accumulated watch time of 23 years – follow a similar formula. Squibb walks up to strangers, asks about their dreams and then offers business advice and sometimes even investment. The format has struck a chord with younger generations. But unlike most full-time influencers, Squibb is not motivated by money or fame. Not only did he achieve financial freedom and retire with his wife a decade ago, but he also finds fame more burdensome than enjoyable. “Being famous is not a good idea – but if you have a purpose, the influence is totally worth it. I love the influence. I hate the fame,” Squibb says over coffee at Hong Kong’s IFC Mall. “Fame is a sacrifice. People think it’s an asset, but you’re giving up freedom. I’m shocked by how many people recognise me here. I can’t even go to the bathroom without being stopped five times for photos. From an influence standpoint, that’s amazing – but from a life standpoint, it makes things harder.” For Squibb, the sacrifice is justified by a mission: to show how entrepreneurship can help people break free from the exploitative “sell your time for money” system. He hopes to spare others the struggles he faced as a young founder. “I realised the problem in all markets – America, Europe, Hong Kong – is that we don’t teach entrepreneurship in schools. I wanted to fix the education system. That’s why I took social media seriously five years ago,” he says. Squibb’s life could have gone very differently. At 15, he became homeless after his father’s sudden death and a fallout with his mother. With no safety net, he relied on sheer instinct, and his entrepreneurial spirit was born. “I saw a messy garden outside a big house and thought, maybe they’ll pay me to clean it up,” he recalls. That simple idea – knocking on a stranger’s door to offer his services – became his first business. He admits he was a terrible gardener, but he quickly learned to hire others, negotiate and bootstrap his way forward. Decades later, after building and selling multiple companies, Squibb now dedicates his life to helping others do the same. Hong Kong holds a special place in Squibb’s story. It is where he met his wife and co-founded Fluid, a leading creative agency later acquired by the financial services firm PwC. He arrived in Hong Kong just before the 1997 handover, when the city went from British to Chinese sovereignty, and felt an immediate connection. “Hong Kong has no natural resources – everything here was imagined and built by people. That resonated with me deeply,” he says. Through Fluid, he helped local businesses expand globally. Later, as an early-stage investor, he noticed a funding gap for Hong Kong start-ups. “I believed – and still believe – Hong Kong could be the next Silicon Valley.” After selling his businesses and “retiring” at 40, Squibb quickly realised a life of leisure was not for him. “I felt useless,” he says. The birth of his son further fuelled his desire to create a world where young people learn financial literacy and entrepreneurship. Five years ago, he turned to social media to share free business advice. Today, his content reaches more people than many traditional media networks. “Most people are in fight-or-flight mode, just trying to pay bills,” he says. “But if you can imagine a better future, you can make it real.” Squibb began to receive thousands of direct messages a day from people seeking guidance, which led him to think about ways to scale his impact. Recently, he created an AI-powered mentorship app that lets users “call” a digital version of him for free advice. “In just five days, the AI helped 68,000 people,” he says. The app, available on iOS and Android, answers everything from business strategies to personal growth. “It costs me £5,000 [US$6,640] a day to run, but it’s worth it. If someone in Nigeria or India can’t afford a coach, they can still get help.” His other latest venture, HelpBnk, is a platform for freely giving and receiving help. “Humans are wired to help. The poorest people I’ve met in Thailand share their last bowl of rice. If everyone gave just five minutes a day, we could end wars in three weeks.” Earlier this year, he published a book targeting people who prefer to take in his lessons through a more traditional medium. What’s Your Dream consolidates the business lessons that Squibb shares online while also touching upon the more philosophical side of how to overcome fear and self-sabotage. The book made it onto the Sunday Times Bestseller list. “In the book, I try to help people realise what are the subconscious belief systems that we have and how we can remove them,” he says. “Because you won’t be able to have a dream if you genuinely believe that starting a business equals failure. If you believe that in your subconscious, your body won’t even let you do it.” At a recent Hong Kong book signing, he was surprised to see not just young readers but also parents in their fifties. “Usually, it’s young people figuring out their dreams. But this time, I saw parents thinking, ‘I’ve spent my life in a job I didn’t love to pay the mortgage. Now that my kids are grown, what’s my dream?’” He also saw parents recommending the book to their children as a tool to help them achieve their dreams. To Squibb, this shift – from traditional Asian values favouring stability to a generation encouraging their children to pursue dreams – is profound. “The biggest risk is taking no risk at all. If you’re stuck in a job you hate, ask yourself: what would I do if I had US$20 million? Then start doing it today – because you probably don’t need that much money to begin,” he says. He advises to not suppress or be paralysed by fear, but to use it to your advantage. “I’ve realised that fear, it’s a good thing to feel,” he says. “Think of how a lion chasing after you will make you run faster than you could’ve ever imagined. People in modern society try to turn fear off. It’s a mistake. Fear drives you to not fail. Fear drives you to new limits, new abilities that you didn’t even know you had.” Fear was something he himself had to confront and use to his own advantage at the beginning of his social media journey. “When I first made [a] social media [account], I was very scared when I first went online. I was like, ‘Oh I’m a grown up 51-year-old man going on social media. This is embarrassing.’ “I remember sitting at a lunch in Hong Kong with all these people that sold their companies – all very rich people that have done well. We were going around the table sharing what everyone is doing now. “One person was like, ‘Oh I’ve invested in property,’ another said he invested in businesses. I said I am on social media posting about how to start businesses. People were confused and asked what the purpose of that was. “Now they are asking me how to do it.”

Profile | How entrepreneur and social media star Simon Squibb is helping people achieve their dreams

Business advice guru Squibb, for whom Hong Kong played a special part is his story, talks about helping people gain financial freedom